The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans


Mellor, J. M. and El-Sagheer, A. H. (2000) The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans. Tetrahedron Letters, 41, (38), 7387-7390. (doi:10.1016/S0040-4039(00)01256-9).

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Description/Abstract

Readily available cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones react with excess phenyl magnesium bromide by initial 1,4-addition, followed by ring opening to give a variety of products. Both the major products, unsaturated diols, and the minor products, as shown by X-ray diffraction studies, are generated with high stereoselectivity, which is attributed to A(1,3)-strain.

Item Type: Article
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Keywords: allylic strain, grignard reagents, tetrahydropyrans diastereoselective synthesis, allylic 1,3-strain, epoxidation
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19005
Date Deposited: 15 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/19005

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